An unprecedented macrocycles-in-a-macrocycle (MIM) superstructure was formed by reversible radical-radical association of a triphenylamine based monomer terminated with three dicyanomethyl radicals (1). The reaction yield is nearly quantitative and the obtained macrocycle (2) contains three small dimeric macrocycles. The six monomer molecules are linked by nine long dynamic covalent C-C bonds which all adopt a gauche conformation. Two enantiomers with left- / right-handed chirality exist in the single crystals of 2.